title: Manganese(III) complexes of bis(hydroxyphenyl)dipyrromethenes are potent orally active peroxynitrite scavengers.
abstract: We report a new series of biscyclohexano-fused Mn(III) complexes of bis(hydroxyphenyl)dipyrromethenes, 4a-c, as potent and orally active peroxynitrite scavengers. Complexes 4a-c are shown to reduce peroxynitrite through a two-electron mechanism, thereby forming the corresponding Mn(V)O species, which were characterized by UV, NMR, and LC-MS methods. Mn(III) complex 4b and its strained BODIPY analogue 9b were analyzed by X-ray crystallography. Finally, complex 4a is shown to be an orally active and potent analgesic in a model carrageenan-induced hyperalgesia known to be driven by the overproduction of peroxynitrite.
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmacy, Southern Illinois University Edwardsville, Edwardsville, Illinois 62026, USA.
authors.forename: Smita
authors.initials: S
authors.lastname: Rausaria
authors.forename: Andrew
authors.initials: A
authors.lastname: Kamadulski
authors.forename: Nigam P
authors.initials: NP
authors.lastname: Rath
authors.forename: Leesa
authors.initials: L
authors.lastname: Bryant
authors.forename: Zhoumou
authors.initials: Z
authors.lastname: Chen
authors.forename: Daniela
authors.initials: D
authors.lastname: Salvemini
authors.forename: William L
authors.initials: WL
authors.lastname: Neumann
mesh_terms: D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry*; D008345:Manganese / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D030421:Peroxynitrous Acid / Q000737:chemistry*; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D016166:Free Radical Scavengers; D009942:Organometallic Compounds; C559046:bis(hydroxyphenyl)dipyrromethene; D030421:Peroxynitrous Acid; D008345:Manganese; D011162:Porphobilinogen